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- Tasks: Lead and scale the penetration testing function while staying hands-on with technical delivery.
- Company: Dynamic cyber security consultancy focused on offensive security.
- Benefits: Competitive salary of £85,000, hybrid work model, and opportunities for professional growth.
- Other info: Join a growing team and make a real impact in the cyber security landscape.
- Why this job: Shape the future of penetration testing while influencing a talented team.
- Qualifications: Strong background in penetration testing and leadership experience required.
The predicted salary is between 85000 - 85000 £ per year.
We are working with a growing cyber security consultancy looking to hire a Head of Penetration Testing to lead and scale their offensive security capability. This is a hands-on leadership role, ideal for someone from a strong penetration testing background who wants to step into a position where they can own technical delivery, shape a team, and influence the direction of a testing practice - without stepping away from the tools.
The Role: You will take ownership of the organisation's penetration testing function, leading from the front on technical delivery, quality standards, and team development. This role is best suited to someone who is already operating as a Senior / Lead Penetration Tester or CHECK Team Leader, and is looking to step into a broader leadership position while remaining technically hands-on. You will play a key role in defining methodologies, mentoring testers, engaging clients, and driving the growth of the penetration testing offering.
Key Responsibilities:
- Lead and scale the penetration testing function (people, processes, tooling)
- Deliver and oversee high-quality penetration testing engagements (web, infrastructure, cloud, application)
- Act as a technical authority across offensive security engagements
- Ensure consistency and quality across all reports and deliverables
- Support pre-sales, scoping and client engagements
- Mentor and develop a team of penetration testers
- Manage utilisation, capacity, and technical performance of the team
- Contribute to service development and growth of the practice
Key Skills & Experience:
- Strong background in penetration testing (offensive security) across web, infrastructure, and cloud
- Experience operating at Senior / Lead Pen Tester or CHECK Team Leader level
- Hands-on experience delivering client-facing penetration testing engagements
- Strong reporting skills and ability to communicate findings to both technical and non-technical stakeholders
- Experience mentoring or leading testers
- Certifications (essential): Candidates must hold two or more of the following (or equivalent) CREST CRT or CCT, OSCP, OSCE / OSWE, CISSP, CHECK Team Member (CTM) or CHECK Team Leader (CTL)
Why Join?
This is an opportunity to step into a role where you can shape and lead a penetration testing function, not just deliver within one. You will have the autonomy to influence how the practice evolves, while still staying close to the technical work that got you here. If this sounds like you, apply now!
Head of Penetration Testing (Hands-on) employer: Oscar Associates Limited
Contact Detail:
Oscar Associates Limited Recruiting Team
StudySmarter Expert Advice 🤫
We think this is how you could land Head of Penetration Testing (Hands-on)
✨Tip Number 1
Network like a pro! Get out there and connect with folks in the cyber security scene. Attend meetups, conferences, or even online webinars. You never know who might have the inside scoop on that perfect Head of Pen Testing role!
✨Tip Number 2
Show off your skills! Create a portfolio showcasing your penetration testing projects and achievements. This is your chance to demonstrate your hands-on experience and technical prowess, making you stand out from the crowd.
✨Tip Number 3
Prepare for those interviews! Brush up on your technical knowledge and be ready to discuss your past experiences in detail. Practice common interview questions and think about how you can convey your leadership style and mentoring approach.
✨Tip Number 4
Don’t forget to apply through our website! We’ve got loads of opportunities waiting for you, and applying directly can give you a better chance of landing that dream job. Plus, we love seeing candidates who are proactive!
We think you need these skills to ace Head of Penetration Testing (Hands-on)
Some tips for your application 🫡
Tailor Your CV: Make sure your CV reflects the skills and experiences that align with the Head of Penetration Testing role. Highlight your hands-on experience and leadership qualities, as we want to see how you can lead from the front while still being technically involved.
Craft a Compelling Cover Letter: Your cover letter is your chance to shine! Use it to explain why you're the perfect fit for this role. Share specific examples of your past achievements in penetration testing and how you’ve mentored others, as we value those who can inspire and develop a team.
Showcase Your Certifications: Don’t forget to list your relevant certifications prominently. We’re looking for candidates with qualifications like CREST CRT or CCT, OSCP, or CHECK Team Leader, so make sure these are easy to spot in your application.
Apply Through Our Website: We encourage you to apply directly through our website. It’s the best way for us to receive your application and ensures you’re considered for this exciting opportunity to shape our penetration testing function!
How to prepare for a job interview at Oscar Associates Limited
✨Show Off Your Technical Skills
As a Head of Penetration Testing, you need to demonstrate your hands-on experience. Be ready to discuss specific tools and methodologies you've used in past engagements. Prepare examples that showcase your technical prowess and how you've led teams in delivering high-quality results.
✨Communicate Clearly with All Stakeholders
You’ll be expected to communicate findings to both technical and non-technical stakeholders. Practice explaining complex concepts in simple terms. This will not only show your understanding but also your ability to mentor and lead effectively.
✨Prepare for Leadership Questions
Since this role involves leading a team, expect questions about your leadership style and experiences. Think of examples where you've successfully mentored testers or influenced a project’s direction. Highlight your approach to team development and how you ensure quality standards.
✨Engage with the Company’s Vision
Research the consultancy's current penetration testing practices and any recent projects. Be prepared to discuss how you can contribute to their growth and service development. Showing that you understand their goals will set you apart as a candidate who is genuinely interested in the role.